Online booking systems match guests looking for short term accommodation with a listing for accommodations offered by a host. After locating a desired listing, guests contact hosts with inquiries and/or requests to book the desired listing. Guests have certain preferences that impact whether they will move forward to booking after an inquiry or request to book. Similarly, hosts typically have certain preferences that impact whether a particular request for an accommodation is accepted or rejected by them. Such preferences may be explicitly provided by the guests and hosts. Most often, however, the preferences are implicit and dependent upon several variables that are not easily quantifiable. Therefore, it can be difficult to determine whether a particular inquiry for a reservation will result in a booking (i.e., inquiry accepted by the host and then the listing booked by the guest).